Process for coating a substrate with a nitroaryl-sulfonamide-substituted triazine intumescent agent

ABSTRACT

Intumescent compositions of the invention comprise nitroarylsulfonamido-substituted 1,3,5-triazines, such as 2-(pnitrobenzenesulfonamido)-4,6-diamino-1,3,5-triazine. The intumescent agents are employed in a process for protecting a substrate from heat and fire. The intumescent agents may be employed in conjunction with conventional additives.

States Patent [191 {45} Oct. 30, 1973 PROCESS FOR COATING A SUBSTRATE WITH A NITROARYL-SULFONAMIDE- SUBSTITUTED TRIAZINE INTUMESCENT AGENT [75] Inventor: Shirley H. Roth, Highland Park, NJ.

[73] Assignee: Cities Service Company, New York,

22 Filed: Jan. 21, 1972 21 Appl. No.: 219,876

[52] [1.8. CI. 117/136, 106/15 FP, 252/8.1,

117/138.8 B, 117/147 [51] Int. Cl. C0911 5/18 [58] Field 01 Search 260/2466, 246.5,

260/239.7, 397.8; 117/138.8 B, 147, 136; 252/8.1; 106/15 FP [56] References Cited UNITED STATES PATENTS 2,616,866 11/1952 Juda ..l17/136X 2,648,641 8/1953 Robison 117/136 X 2,872,355 2/1959 Muller et a1. 117/136 2,984,640 5/1961 Kaplan 117/136 X 3,635,970 1/1972 Fessler et a1... 260/2496 2,407,177 9/1946 Roblin et a1. 260/239] Primary Examinerwilliam D. Martin Assistant ExaminerTheodore G. Davis AttorneyRichard S. Strickler, Elton F. Gunn, Patricia J. Hogan, Burton E. Levine, Joshua J. Ward, Edwin T. Yates, George L. Rushton and A. Joe Reinert [5 7] ABSTRACT 3 Claims, No Drawings PROCESS FOR COATING A SUBSTRATE WITH A NITROARYL-SULFONAMIDE-SUBSTITUTED TRIAZINE INTUMESCENT AGENT BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to intumescent compositions and more particularly relates to such compositions containing a one-component intumescent agent.

2. Description of the Prior Art It is known that a substrate may be protected from heat and tire by the application of an intumescent composition. Intumescent compositions of the prior art usually contain an intumescent agent having at least three components, i.e., a carbonific, a spumific, and a catalyst; and they are typically characterized by the disadvantages of high cost, low spreading rate, relatively poor efficiency, poor water resistance, and poor weatherability.

As disclosed in U. S. Pat. No. 3,535,130, it has already been discovered that a one-component intumescent agent has advantages over multicomponent intumescent agents. However, the intumescent agents of the patent have poor adherence to substrates and have an undesirable degree of moisture sensitivity.

SUMMARY OF THE INVENTION An object of this invention is to provide a novel class of one-component intumescent agents.

Another object is to provide such intumescent agents having good efficiency and a low level of moisture sensitivity.

These and other objects are attained by using as intumescent agents compounds corresponding to the formula:

wherein Ar is a divalent aromatic hydrocarbon or halohydrocarbon residue and X is amino, hydroxy, halo, or

DESCRIPTION OF THE PREFERRED EMBODIMENTS The intumescent agents of the invention may be any compounds corresponding to the above formula. However, they are preferably compounds wherein Ar is a divalent aromatic residue derived from benzene or naphthalene or a halo or haloalkyl derivative thereof. When there are halo substituents on the aromatic or triazine ring, it is usually preferred that they be chloro or bromo. It is also preferred that the aromatic ring have at least one free reactive position.

Exemplary of the intumescent agents of the invention are 2-(p-nitrobenzenesulfonamido)-4,6-diamino-l ,3 ,5- triazine, 2-(o-nitrobenzenesulfonamido)-4,6-diamino- 1,3 ,S-triazine, 2-(m-nitrobenzenesulfonamido)-4,6- diaminol ,3,5-triazine, 2 3-chloro-4- nitrobenzenesulfonamido )-4,6-diamino-l ,3 ,S-triazine, 2-(4-bromo-2-nitrobenzenesulfonamido)-4,6-diaminol,3,5-triazine, 2-( 3-nitro-4- trichloromethylbenzenesulfonamido )-4 ,-diaminol,3,5-triazine, 2-(p-nitrobenzenesulfonamido)-4,6- dihydroxyl ,3 ,S-triazine, Z-(p-nitrobenzenesulfonamido)-4,6-dichloro-l ,3,5-triazine, Z-(p-nitrobenzenesulfonamido)-4,6-dibromo-l ,3,5-triazine, 2,4-bis(pnitrobenzenesulfonamido)-6-amino l ,3,5-triazine, 2,4- ,6-tris(p-nitrobenzenesulfonamido)- l ,3,5-triazine, the corresponding nitronaphthalenesulfonamido compounds, etc. The preferred intumescent agents include 2-(p-nitrobenzenesulfonamido )-4,6-diamino-l ,3 ,5- triazine, 2,4-bis(p-nitrobenzenesulfonamido )-6 -aminol,3,5-tri-azine, and 2,4,6-tris(p-nitrobenzenesulfonamido)-l,3,5-triazine. When not readily available, these compounds may be prepared by known techniques.

For use in protecting a substrate from heat and fire, the intumescent agents of the invention may be applied in any suitable manner, e.g., electro-deposition, spraying of powdered intumescent agent onto an adhesive substrate, etc. However, it is usually preferred to compound the intumescent agent with a binder, e.g., nitrocellulose, and optionally also with one or more of theother ingredients conventionally used in intumescent compositions, e.g., stabilizers, dispersing agents, pigments, driers, biocides, anti-foamers, thickeners, protective colloids, fillers, blowing agents, etc.; disperse the composition in a suitable liquid medium, e.g., water or a solvent or solvent mixture; and apply the coating composition thus formed to the substrate to be protected. As is the case with conventional intumescent coating compositions, it is frequently convenient to apply these coating compositions in the form of a paint having a solids content of about 10-70 percent by weight and an intumescent agent/binder weight ratio of about 0.075l4/l to deposit a coating having a dry thickness of about 0.001-0.75 inch.

The intumescent agents of the invention are efficient, have low moisture sensitivity, and intumesce without flaming to form foams having good volume, cell structure, and adherence to substrates, such as wood, metal, and plastics. They are also useful as flame retardants in normally flammable compositions.

The following examples are given to illustrate the in vention and are not intended as a limitation thereof.

EXAMPLE I EXAMPLE II Repeat Example I except for substituting 2,4-bis(pnitrobenzenesulfonamido)-6-amino-l ,3,5-triazine and 2,4,6-tris(p-nitrobenzenesulfonamido)- l ,3 ,5-triazine, respectively, for the 2-(p-nitrobenzenesulfonamido)- Similar results are obwherein Ar is a divalent aromatic hydrocarbon or halohydrocarbon residue and X is amino, hydroxy, halo, or

2. The process of claim 1 wherein Ar is a divalent aromatic residue derived from benzene.

3. The process of claim 2 wherein the intumescent agent is 2-(p-nitrobenzenesulfonamido)-4,6-diaminol ,3,5-triazine. 

2. The process of claim 1 wherein Ar is a divalent aromatic residue derived from benzene.
 3. The process of claim 2 wherein the intumescent agent is 2-(p-nitrobenzenesulfonamido)-4,6-diamino-1,3,5-triazine. 